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Dear Former Friend,
I say “former” because “ex” makes it sound like there’s a romantic element, and while there was a time when I would have liked to have a downstairs party with you, that was a loooong time ago.
We decided to go the “just friends” route.
Then I realized that I didn’t have much interest in being friends, either… I mean, sure, we hung out some times, but most of your texts were spent calling me “missy” and other effeminate names which is, well, it’s a solid joke to start with, but it wears after seven months.
Still, I’m sorry we ended our friendship the way we did.
Cuz, like, now I’m remembering that time you made fun of that homeless man? The one who was diabetic and lost a foot?
Yeah, I’m mainly sorry cuz I shoulda ended this friendship sooner.
Sincerely,
Calhoun

Dear Guy,
I know we’ve had our fair share of ups and downs since we’ve known each other.
I know neither of us is quick to trust or communicate our feelings.
But I also know that if I could do anything (and I mean anything) all I wanna do is fix you.
You’re not broken, per se, but life hasn’t always been kind to you.
You’re not great with trust because no one has given you a reason to trust.
I’d like to be that reason.
I know these are just words so it might not count for much, but it’s pretty much all I’ve got.
I love you.
Sincerely,
Calhoun

Dear Ex,
A lot has changed since we broke up.
I mean, yes, we still kiss when we see each other.
And yes, we still have sex.
Okay, there’s also that other thing where we still tell each other “I love you” at the beginning and end of every conversation.
Then there’s the whole, “I haven’t slept with anyone else and neither have you.”
… wait, we did break up, right?
I mean, you were the one who wanted to break up and- well, I just feel like we could use some work on our follow-through here.
Sincerely,
Calhoun

Dear Hook-Ups,
Do you know what it means to be a hook-up?
I mean, I <i.think ya do, and I’m trying to keep it… well, would you believe me if i said PG-13?
No I do not want you to ask me how my day was, nor do I want to hear about your niece’s dance recital.
I mean, c’mon, you’re kinda ruining it over here… now I hafta think about you as, ya know… a person.
Okay, that came out wrong. You’re a person. I take it back, you’ve always been a person.
Maybe not a person I was interested in sitting down and having a coffee with, but yes, a person nonetheless.
I just meant… Jesus, what did I mean?
I guess I just meant, maybe we can save the feelings stuff for your therapist and not the guy you just, ya know… met?
That’d be just great, thanks.
Sincerely,
Calhoun

Dear LA,
It’s been real, but I think the time has come for us to split ways.
Normally, I would say “it’s not you, it’s me.” Hell, more often than not, it’s not even a lazy cliché I’m using.
It usually is my fault.
But this time? This time it’s on you.
If it’s not smog, it’s superficiality.
If it’s not pointless conversations about organic produce, it’s an equally meaningless discussion of who knows whom.
If it’s not endless traffic, it’s… well, you get my point.
But I don’t think this is entirely one-sided. I think, whether you admit it now or not, you’ll be glad to be rid of me, LA.
Hopefully we can both grow from this experience.
Sincerely,
Calhoun

Dear Random Guy at IKEA,
I swear, I wasn’t stalking. Like, pinky swear. In fact, if we’re gonna play that game, you may have entered IKEA before us, but you were behind us every step of the way, including our unplanned stop for Swedish meatballs.
Anyways, you may have noticed that I was trying not to stare. I’m not very good at that.
But whenever I would look, you would smile so I figured it wasn’t too terrible.
That being said, I wish our taciturn relationship had lasted a little longer, but what can I say?
Like Vince Vaughan and every other improbable male lead in a romantic comedy, I’m afraid of commitment.
35 minutes was a good run for us. The knowing smile at the end? Like something out of an overrated Sofia Coppola movie?
That was my favorite part.
But take comfort in knowing, it wasn’t you, it was me. Actually, it was a little bit you.
You spent half of our relationship looking at drapes. I mean, what the hell?
Still, I wish you all the best and hope you find happiness at the next store. Maybe a Crate & Barrel or The Container Store?
Just some helpful suggestions, I wanna see you happy.
Well, we had a good run, but I should probably go.
Take care of yourself.
Sincerely,
Calhoun

Dear Nice Guy,
Everybody likes you. No, seriously. You have what most of us have, and that is the insatiable and borderline pathological need to be liked. Don’t feel bad. I’m the same way.
The only thing is, well, I’m realistic. I realize that, whether I like it or not, there are bound to be times where I am not well-liked.
So when you gave me the “just friends” speech? Totally fine.
Would I have liked a little more originality? Sure, but what are you gonna do about it.
It was the incessant “sorry” at the end of every sentence from you.
You don’t have to apologize for feeling the way you feel.
But “sorry” never feels like a genuine sorry. It usually comes out as “sorry you probably think I’m a dick right now.”
I don’t. You’re not. But please, quit trying to be the nice guy in a pseudo-breakup.
I just really need to not like you for five minutes.
Sincerely,
Calhoun